Doing It for the People: The 25 Greatest Philanderers in American Political History

25. Dwight D. Eisenhower

President, Redhead Enthusiast

Ike met Kay Summersby, a former model and actress, when she was assigned to be his driver in 1942. The lively redhead (who had a "reputation" in England) became his full-time chauffeur shortly after, moving with him to Algiers and escorting him during his visits to the front lines. "Fearless" in her work, Kay also rode horses with Ike, served as his on-base hostess, and shared his meals. Their closeness escaped no one's attention, though Ike wrote Mamie—in notably specific terms—that he had "no emotional involvements" with Kay. Riiiiight.

24. David Vitter

Devout Christian, Call-Girl Authority

In 2007, when the Louisiana senator's phone number was found in the call logs of a company owned and operated by Deborah Jane Palfrey—the "D.C. Madam"—he gave a press conference in which he insisted the matter was between him, God, and his family, though presumably at least one other person was involved. The logs showed the escort agency called Vitter five times, twice when congressional records show a vote to be in progress. Talk about voting "Yea!"

Like a good conservative, Ensign chose his Washington mistress the old-fashioned way: She was the wife of his employee. Upon discovering the affair in 2009, cuckolded husband Douglas Hampton confronted Ensign, who responded like any good capitalist would: He started steering lucrative lobbyist work Hampton's way. Then Ensign's parents gave Hampton and his family $96,000, apparently just for being awesome. Ensign lived in Washington in a group home for male Christian politicians where the fellowship meetings are probably more exciting than you'd think.

21. Roscoe Conkling

Senator and Surprisingly Fast Runner

After years of carrying on a widely discussed affair with Kate Chase Sprague, Conkling must have been as surprised as William Sprague when they ran into each other at Sprague's Rhode Island home in 1879. But what Kate's spouse lacked in suspicion he more than made up for with firepower. As The New York Times reported at the time of Sprague's death, upon spotting Conkling, Sprague "grabbed up a shotgun and pursued."

20. Bob Livingston

Larry Flynt Victim

Livingston left the Speaker of the House designate position about two seconds after he arrived in 1998, thanks to Larry Flynt, who claimed to have found evidence of four extramarital affairs. Livingston called for Bill Clinton to follow his example, though when you think about it, he probably should have followed Clinton's. His seat was filled by David Vitter and, like, wow—is there something in the water down there?

19. Newt Gingrich

"Republican Revolution" Leader, Hobbit

He may resemble a particularly unattractive hobbit, but Gingrich is on wife number three, so he's doing something right. No, wait. Hang on a second. He's doing everything wrong. He left Wife One while she was fighting cancer, telling her he was leaving her for Wife Two while she was in the hospital. He left Wife Two after cheating on her with Wife Three while he was leading the charge to impeach President Clinton. Asked if that behavior made him a hypocrite, Gingrich admitted it did. Just kidding! He insisted that calling for impeachment did not mean he was "rendering judgment."

18. Don Sherwood

Failed Masseur

In September 2004, Cynthia Ore called 911 from inside the locked bathroom of Sherwood's Washington apartment. Ore accused the Republican congressman of choking her; Sherwood insisted he was only giving her a back rub. No charges were filed, but Sherwood's 2006 reelection campaign forced him to deal with the issue, and eventually he recorded an ad in which he expressed sorrow for "disappointing you" but contended that he still wanted to "reduce tas." He lost.

17. Wayne Hays

Democratic Congressman and Lousy Boss

Divorced his wife of thirty-eight years to marry his secretary, much to the surprise of his lover, Elizabeth Ray, who was on his congressional staff. Ray then revealed to The Washington Post in 1976 that her sole duty was to be Hays's lover: "I can't type, I can't file, I can't even answer the phone." Lawyers' investigation as to whether Hays did anything illegal in employing Ray came to naught when Ray turned out to be as solid a witness as she was a typist.

16. Estes Kefauver

Infamous Lover of the Ladies

Best known for the 1950s Senate hearings that brought the Mob to popular attention, Kefauver was a notorious womanizer and drinker, supposedly yelling, "I gotta fuck!" on the way out of a bus after a campaign trip. One FBI source said that the Democrat "made love in plain view" with his date at a Mayflower Hotel party, only to trade women with JFK afterward. He also led a campaign against the corrupting effect of sexualized, violent comic books. Indeed.

15. Strom Thurmond

Senator, Civil Rights Pioneer

Back when the continents were forming, Thurmond participated in a common pastime of the white folk in the South: getting a black maid pregnant. Thurmond did not follow through on the second part of that tradition: ignoring the child. He paid for his daughter's education and gave her money regularly. He just never told anyone why.

14. Jon Hinson

Public-Nudity Advocate

Elected to Congress in 1978, Hinson admitted in 1980 that, two years earlier, he had exposed himself to an undercover policeman and been arrested at the Iwo Jima Memorial. (Because there's nothing hotter to a Republican than raising the American flag.) Hinson insisted, however, that he was not gay—just drunk. He won reelection but was arrested again in 1981 after he was caught performing oral sex on a Library of Congress employee in a restroom. After resigning he became a gay activist fighting for the right of out homosexuals to serve in the military. So good came out of it after all.

13. Gary Hart

Laughably Self-Destructive Candidate

The person Washingtonians picture when they think of hubris. Basically dared reporters to prove he was having an affair in 1984, and then, hey, they did! And from then on, no one in Washington asked for proof of anything—except if Hart had actually been a passenger on a yacht called Monkey Business when a photographer snapped the incriminating picture that ruined his career. Because, man, twenty-plus years later and that's still hard to believe.

12. Eleanor and Franklin D. Roosevelt

Platonic Power Couple

The swingingest duo to ever occupy the White House, FDR and Eleanor each seemed to have had at least one affair with a woman. The first lady discovered love letters between Franklin and Lucy Mercer, Eleanor's former social secretary, in 1918, and from then on the Roosevelts had a largely platonic relationship. (Lucy was given her own Secret Service code name and was with FDR when he died in 1945.) Eleanor's love life remains more mysterious, though her relationship with reporter Lorena Hickok was unusually close. Eleanor wrote about wanting to "kiss hold" Hickok.

11. Thomas Jefferson

Randy American Icon

The man treated his slaves very well. Let's just leave it at that kind of disgusting irony.

10. Warren Harding

Epically Terrible and Extremely Horny President

His charms are obscure to modernday women but appear to have been very effective. Harding carried on a fifteenyear tryst with Carry Fulton Phillips that paused briefly when Harding voted to support World War I and ended after Harding became a presidential nominee, when the inconvenient Phillips and her family were sent to Japan "to investigate the silk trade." Harding also romanced Nan Britton, a stalker-y girl whose crush on him started when she was 14. As a young woman, she pasted pictures of Harding on her bedroom walls. Harding apparently did not find this weird at all and, so Britton claimed, started sleeping with her seven years later.

9. Alexander Hamilton

Duelist, Philanderer, Founding Father

His affair and its aftermath reveal the starkest differences between the Washingtons of the eighteenth century and now. After being accused of embezzlement and involvement with an unsavory character named James Reynolds, Hamilton protested his innocence by explaining that his connection with Reynolds wasn't that they were cheating the government together—he was just banging Reynolds's wife. There is some question whether the public confession—considered bizarre at the time—was used to cover up an actual crime, a sort of Whitewater scandal in perfect reverse.

8. Wilbur Mills

Arkansas Congressman, Burlesque Devotee

In October 1974, Washington, D.C., United States Park Police stopped Mills for cruising near the Jefferson Memorial, only to have stripper Fanne Fo, a.k.a. the Argentine Firecracker, pop out of the passenger seat and attempt to escape by jumping into the Tidal Basin. Mills ultimately confessed to being an alcoholic and never ran for office again, instead forging a career as an addiction counselor and teller of this cautionary tale: "I had President Ford convinced on national health [care], but I couldn't get the committee to go with me. It was because of my drinking they didn't."

7. William Breckinridge

Reconstruction-Era Rake

The original Slick Willie had been in Congress nine years before his longtime lover, Madeline Pollard, sued for "breach of promise." She claimed to have been made pregnant by him three times and that he'd asked her to marry him—but when Breckinridge's wife died, the congressman asked his cousin for her hand instead. Pollard sued, and witnesses told stories so racy the judge actually barred women from the courtroom. As for poor Mr. Breckinridge? He never held elected office again.

6. John Edwards

Vice Presidential Candidate, National Disgrace

If you don't know why he's on here, please close this browser window and back slowly away into a bed full of teddy bears.

5. Alice Roosevelt Longworth and Nick Longworth

Republican Superfreaks

Alice and Nick had what people used to call an understanding and now just call a reality show. The couple married at the White House and carried on simultaneous affairs, with Nick committing an additional apostasy by supporting William Taft over Alice's father, Teddy, in 1912. But it's Alice who deserves special note: She bore a daughter to Senator William Borah even as the senator, also married, simultaneously carried on an affair with publishing heiress Eleanor Medill Patterson. This led to one of D.C.'s sharpest sublimated rivalries: Legend has it that after hosting both Borah and Patterson at a party, Alice returned a set of hairpins to Patterson with the note "I believe they are yours." Patterson supposedly replied, "And if you look up in the chandelier, you might find my panties."

4. Bill Clinton

Intern Mentor

It's a testament to Clinton's all-toosubstantial charm that Washington's most famous philandering pol retains, well, all the power and influence any ex-president can expect. Actually, he probably gets as much of everything as any ex-president can expect, if stories linking him to a Canadian billionairess…and the daughter of a top Democratic donor in Michigan…and half of the state of Arkansas can be believed.

3. Arthur Brown

Shooting Victim

One of Utah's first senators, and without a doubt the most exciting. He died of a gunshot wound inflicted by his mistress, Anne Bradley. Brown had recently been widowed, and Bradley apparently expected to take his late wife's place. But as one account puts it, "He was in no hurry to gain legal access to what he had enjoyed illicitly." When Bradley traveled to Washington in 1906 only to find letters between Brown and another woman, well, then—bang bang. At the trial, Bradley pleaded temporary insanity; she was acquitted.

2. Ben Franklin

Founding Father and Sexual Badass

Bespectacled, paunchy, inventor of shit like the wood-burning stove, and total mack daddy. Franklin had several lady friends in France and a child out of wedlock; his confidence in his game prompted the short essay "Advice to a Young Man on the Choice of a Mistress," which encourages aspiring Romeos to catch cougars for a whole host of reasons, including "they are so grateful."

1. John F. Kennedy and Robert F. Kennedy

American Icons, Cheating Hall of Famers

Jack's dalliances with the famous (Marilyn Monroe) and infamous (mobster moll Judith Exner) are only the lightest shades of Camelot's darker side. JFK supposedly took girls to the White House pool for sex, and a recent book asserts RFK romanced a mourning Jackie aboard the presidential yacht. As for Teddy, magazine law dictates that we wait five years, or two tell-all books, before including him on this list.